1. Discuss Omar's decision to travel to Ochos Rios without sending advance notice. Is spontaneity part of his character? What other factors are behind the decision? Compare and contrast Omar before and after his journey-what's changed about him; what's stayed the same?

2. Discuss the relationship between Caroline and Arden. What are their similarities and differences? Is there significance in the fact that the wife and mistress of the same man live under the same roof?

3. Throughout the novel, Caroline proves herself adept at making others question themselves and their motives. At one point, she forces Omar to confront his entire mission: "But I am not a bad person, Omar told himself. I have no ill intentions. What I want to do is perfectly acceptable and morally innocuous. He put his face in his hands. But why did God invent Caroline?" (Chapter 11) Does Caroline's rigidness help or harm Omar? Is her skill at disarming people effective with all characters in the novel? How does Adam react to her? What about Arden?

4. Initially, each member of the Gund literary estate has their own individual reasons to support or withhold authorization of Jules' biography. What do these reasons say about each individual's character? What motivates each to withhold or support as they do? Of the three members of the Gund family, who carries the most weight, in your opinion, in deciding for or against the biography?

5. In considering her actions throughout the entirety of the novel, what is your opinion of Deirdre? Do you think that her motives for pushing Omar to go to Uruguay were legitimate? What was the turning point of her relationship with him, which eventually lead to their break-up?

6. Delve a bit into the author's writing style. You may want to consider a scene from Caroline's return to New York City (chapter 23) or when Pete brings Omar and Deirdre to Tacuarembó on their way home (chapter 19 ). How do these characters' inner monologues bring out larger themes and issues in the novel?

7. At one point in the novel Omar claims that there can never be a truly "objective" biography, and that "biography is a hoax" (chapter 7). What does he mean by these statements? Do you agree or disagree with his belief? Discuss the role of biography in novel; how does Omar's desire to write a biography affect the members of the Gund family?

8. Consider the author's choice of locales for the novel: Uruguay, Kansas, New York City (and to a lesser extent Germany and England). How does location figure in the events of The City of Your Final Destination? What if Omar had come from a different university? What if the Gund family lived in the United States?

9. Discuss the role of each of the male characters in the novel: Pete, Adam, Dr. Peni and Omar. Whom among these do you find the most intriguing? Do you feel that any of these men are satisfied or truly happy with their lives?

10.Discuss the scene in chapter 10, wherein Adam Gund reflects upon the loss of beauty and charm with age: "There is something a little pathetic about ending up old and beautiful and charming, I think; it indicates, to me at least, a waste of resources, or at the very least, a serious misappropriation of them. For charm and beauty are more valuable commodities in the young. There's little the ancient can buy with them." Could this be construed as a criticism of other characters in the novel? Why or why not? Are the others affected by Adam's pronouncements? How is he different from the other inhabitants of Ochos Rios?

11. What role, if any, does symbolism play in The City of Your Final Destination? Discuss among the group, for example, the role of the gondola, or Omar's fall from the tree, or Caroline's "tower." What deeper meanings could these events or items hold?

12. Should Omar have, in the end, written Jules Gund's biography? What do you think would be some possible outcomes of the novel, of Omar's life and the lives of the Gund group, if he proceeded and did write the biography?

13. Pete, Adam's faithful yet restless companion, plays a unique role in the novel. What's your opinion of Adam's relationship with Pete? Where do you see Pete going in the future?

14. Children often provide objective insights into a person's character. Consider Portia's relationships with the individuals in the novel. What truths does she reveal about them?

15. If you could write a biography of one character from The City of Your Final Destination, who would it be? Why?